[(3aR,4S,5R,6S,7S,7aR)-6-ethenyl-7-hydroxy-6-methyl-3-methylidene-2-oxo-5-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: 65685e4b-c023-4789-b22c-005ef16e08e8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aR,4S,5R,6S,7S,7aR)-6-ethenyl-7-hydroxy-6-methyl-3-methylidene-2-oxo-5-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OC1C2C(C(C(C1C(=C)C=O)(C)C=C)O)OC(=O)C2=C
• SMILES (Isomeric): CC(=C)C(=O)O[C@@H]1[C@@H]2[C@H]([C@H]([C@@]([C@@H]1C(=C)C=O)(C)C=C)O)OC(=O)C2=C
• InChI: InChI=1S/C19H22O6/c1-7-19(6)13(10(4)8-20)14(24-17(22)9(2)3)12-11(5)18(23)25-15(12)16(19)21/h7-8,12-16,21H,1-2,4-5H2,3,6H3/t12-,13-,14-,15-,16-,19+/m1/s1
• InChI Key: PEMWDHVMSOZBIA-MEVSORIUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9793	97.93%
Caco-2	-	0.6882	68.82%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6698	66.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8536	85.36%
OATP1B3 inhibitior	+	0.9106	91.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9390	93.90%
P-glycoprotein inhibitior	-	0.7236	72.36%
P-glycoprotein substrate	-	0.7265	72.65%
CYP3A4 substrate	+	0.6199	61.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	-	0.6818	68.18%
CYP2C9 inhibition	-	0.9311	93.11%
CYP2C19 inhibition	-	0.8835	88.35%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.8318	83.18%
CYP2C8 inhibition	-	0.7835	78.35%
CYP inhibitory promiscuity	-	0.8066	80.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4412	44.12%
Eye corrosion	-	0.9258	92.58%
Eye irritation	-	0.9252	92.52%
Skin irritation	-	0.5537	55.37%
Skin corrosion	-	0.8978	89.78%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5744	57.44%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6658	66.58%
skin sensitisation	-	0.5730	57.30%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.8730	87.30%
Acute Oral Toxicity (c)	III	0.4346	43.46%
Estrogen receptor binding	+	0.6899	68.99%
Androgen receptor binding	+	0.5380	53.80%
Thyroid receptor binding	+	0.5883	58.83%
Glucocorticoid receptor binding	-	0.5499	54.99%
Aromatase binding	-	0.5328	53.28%
PPAR gamma	+	0.6002	60.02%
Honey bee toxicity	-	0.6189	61.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9648	96.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.35%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.50%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.99%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.82%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.66%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.29%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.52%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.99%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.98%	95.50%

Plants that contains it

• Zinnia elegans

Cross-Links

• PubChem: 163096849
• LOTUS: LTS0155646
• wikiData: Q105207190